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Design, Synthesis of Some New Scaffolds based on Pyrrolyl-Pyridines as Potential Anticancer Agents
Corresponding Author(s) : Venkata Nagendra Kumar Putta
Asian Journal of Chemistry,
Vol. 35 No. 2 (2023): Vol 35 Issue 2, 2023
Abstract
Pyrrolyl-pyridine heterocyclic compounds have received considerable attention because of its unique bioisosteric properties and an unusually wide spectrum of biological activities. Thus, it is a perfect framework for the synthesis of novel C–N, C–C bond formations like 5-substituted-1-benzyl-1H-pyrrolo[ 2,3-b]pyridines (3), 2-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenol (5) and screened for their anticancer activity. The synthesized compounds were characterized by 1H NMR, 13C NMR, IR, mass spectral techniques and elemental analysis. The outcomes of these compounds 2,6-difluorobenzyl-pyrrolidin-1H-pyrrolo[2,3-b]pyridine, 2,6-difluorobenzyl-N,N-dimethyl-1H-pyrrolo[2,3-b]-pyridin-5-amine had a signicant anticancer activity against human cervical cancer cell line (Hela) with IC50 4.8, 9.7 μg/mL and whereas pyrrolo[2,3-b]pyridin-5-phenol, pyrrolo[2,3-b]pyridin-5-vinylphenol are active against human breast cancer cell line (MCF-7) with IC50 8.1, 3.2 μg/mL, respectively.
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M. Greenwell and P.K.S.M. Rahman, Int. J. Pharm. Sci. Res., 6, 4103 (2015).
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D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev., 103, 893 (2003); https://doi.org/10.1021/cr020033s
D.R. Motati, R. Amaradhi and T. Ganesh, Org. Chem. Front., 8, 466 (2021); https://doi.org/10.1039/D0QO01079K
V. Sharma, P. Kumar and D. Pathak, J. Heterocycl. Chem., 47, 491 (2010); https://doi.org/10.1002/jhet.349
H.J. Schäfer, C.R. Chim., 14, 745 (2011); https://doi.org/10.1016/j.crci.2011.01.002
J.Y. Merour and B. Joseph, Curr. Org. Chem., 5, 471 (2001); https://doi.org/10.2174/1385272013375427
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S.S. Fatahala, S. Hasabelnaby, A. Goudah, G. Mahmoud and R.H. Abd El Hameed, Molecules, 22, 461 (2017); https://doi.org/10.3390/molecules22030461
S. Narva, S. Chitti, B.R. Bala, M. Alvala, N. Jain and V.G.C.S. Kondapalli, Eur. J. Med. Chem., 114, 220 (2016); https://doi.org/10.1016/j.ejmech.2016.02.059
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B. Blass, ACS Med. Chem. Lett., 6, 726 (2015); https://doi.org/10.1021/acsmedchemlett.5b00185
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